85937-41-3

Upstream product

• 5465-90-7 N-(4-chlorophenyl)glycine 
• 67-64-1 acetone 
• 627-27-0 homoalylic alcohol 
• 106-47-8 4-chloro-aniline 
• 78-94-4 methyl vinyl ketone 
• 590-90-9 1-Hydroxy-3-butanone 
• 598-32-3 2-hydroxy-3-butene 
• 50-00-0 formaldehyd 
• 116-11-0 2-Methoxypropene 
• 3299-38-5 4-(diethylamino)butan-2-one 
• 20265-96-7 p-chloroaniline hydrochloride 

Relevant academic research and scientific papers

Iron powder and tin/tin chloride as new reducing agents of Meerwein arylation reaction with unexpected recycling to anilines

Simple and rapid route for Meerwein arylation reaction using iron powder or a mixture of tin/tin chloride has been developed. In the presence of iron powder, different aryl diazonium salts reacted with methyl vinyl ketone, acrylates, and isopropenyl acetate. Production of oximes was detected as the main product with acrylates or in a mixture with β-aryl methyl ketones in the case of methyl vinyl ketone. The in situ produced HNO2 from an excess of NaNO2/HCl was trapped by alkyl aryl radical to form oximes in the E configuration form. The presence of tin/tin chloride mixture in the reaction of the aryl diazonium salts with methyl vinyl ketone produced Michael products along with β-aryl methyl ketones. The predicted α-aryl methyl ketones from the reaction of isopropenyl acetate with the diazotized anilines were obtained using iron or tin/tin chloride mixture.

Biocatalytic Aza-Michael Addition of Aromatic Amines to Enone Using α-Amylase in Water

The Michael addition of amines with enones for synthesizing β-amino carbonyls constitutes a valuable transformation in organic chemistry. While various catalyst have been made available for catalyzing the Michael addition of aromatic amines to enones but

Method for generating beta-amino ketone compounds through iodine catalysis

The invention discloses a method for generating beta-amino ketone compounds by catalyzing 4-hydroxy-2-butanone to react with aromatic amine through iodine. The method comprises the following steps: taking 4-hydroxy-2-butanone and different aromatic amines as reaction substrates, taking iodine as a catalyst, and dimethyl sulfoxide or N,N-dimethyl formamide as a solvent, and reacting at room temperature in a nitrogen atmosphere to obtain the beta-amino ketone compounds, wherein other byproducts are undetected. By adopting the preparation method disclosed by the invention, the beta-amino ketone compounds can be generated by catalyzing 4-hydroxy-2-butanoe to react with aromatic amine through the iodine at room temperature for the first time.

Iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to form β-aminoketones and Benzo[h]quinolones

An iodine-catalyzed coupling of β-hydroxyketones with aromatic amines to yield β-aminoketones and benzo[h]quinolones had been developed. Noble metallic catalysts, oxidants, α β-unsaturated ketone intermediates and aza-Michael addition were not involved in this coupling reaction which made it unique when compared to other reactions reported in literature. Inexpensive iodine catalyst, easy accessible raw materials, mild reaction conditions, good functional group tolerance and excellent selectivity made this coupling reaction be a practical method. This reaction can also be scaled up.

TBN-Catalyzed Dehydrative N-Alkylation of Anilines with 4-Hydroxybutan-2-one

Until now, the substitution of alcohols by N-nucleophiles via TBN-catalyzed dehydrogenation was not known. Herein, we reported a TBN catalyzed dehydrative N-alkylation of anilines with 4-hydroxybutan-2-one in the presence of TEMPO, which was different from the TEMPO/TBN catalyzed oxidation reactions. A range of anilines reacted successfully with 4-hydroxybutan-2-one to generate the N-monoalkylation products in good yields. Mechanistic studies revealed that this reaction most possibly proceeded through aza-Michael addition. Water was the only by-product, making it more environmentally friendly. The gram-scale reactions verified the synthetic practicality of this protocol.

Method for catalyzing N-alkylation reaction by TEMPO and TBN

The invention discloses a method for catalyzing N-alkylation reaction of aniline and 4-hydroxy-2-butanone by TEMPO and TBN. 4-hydroxy-2-butanone and different anilines are used as the reaction substrate, TEMPO (2,2,6,6-tetramethylpiperidine oxide) is used as catalyst, TBN (tert-butyl nitrite) is used as cocatalyst, dimethyl sulfoxide or N,N-dimethylformamide or toluene is used as solvent, N-alkylation product is obtained in nitrogen atmosphere at room temperature, no other by-products are detected. The preparation method of the invention uses TEMPO and TBN to catalyze aniline compounds and 4-hydroxy-2-butanone to perform N-alkylation reaction.

Palladium-catalyzed aerobic oxidative coupling of allylic alcohols with anilines in the synthesis of nitrogen heterocycles

We report herein an unprecedented and expedient Pd-catalyzed oxidative coupling of allyl alcohols with anilines to afford β-amino ketones which are converted into substituted quinolines in a one-pot fashion. The exclusive preference for N-alkylation over N-allylation makes this approach unique when compared to those reported in literature. Detailed mechanistic investigations reveal that the conjugate addition pathway was the predominant one over the allylic amination pathway. The notable aspects of the present approach are the use of readily available, bench-stable allyl alcohols and molecular oxygen as the terminal oxidant, in the process dispensing the need for unstable and costly enones. Further, we explored the synthetic utility of β-amino ketones through an intramolecular α-arylation methodology and a one-pot domino annulation, thereby providing rapid access to indolines and quinolines.

Palladium-catalyzed oxidative amination of homoallylic alcohols: Sequentially installing carbonyl and amino groups along an alkyl chain

A novel Pd-catalyzed intermolecular cascade oxidative amination of homoallylic alcohols to yield β-amino ketones has been developed by using TBHP as the terminal oxidant. The synthetic utility of the reaction can be performed by installing the carbonyl an

Amphiphilic methyleneamino synthon through organic dye catalyzed- decarboxylative aminoalkylation

The utilization of a photo-induced synthon generated from N-phenyl glycine by an organic dye and visible light irradiation is disclosed. The intermediate could be coupled with either a radical or a nucleophile in a simple operation to afford several natural product-like compounds.

Boric acid/glycerol as an efficient catalyst for synthesis of thiomorpholine 1,1-dioxide by double michael addition reaction in water

Thiomorpholine 1,1-dioxides were prepared with double Michael addition reaction of aromatic amines to divinyl sulfone catalyzed by boric acid/glycerol in water. This catalyst system was also used for the Michael addition reaction of aromatic amines to electron-deficient alkenes. The reaction is simple and green and gives good to excellent yields.